Handsome Boy Modeling School was a conceptual hip-hop duo that parodied and acted as a commentary on vain, crass, materialistic, and self-absorbed members of upper class society, such as supermodels and people from old
... Handsome Boy Modeling School was a conceptual hip-hop duo that parodied and acted as a commentary on vain, crass, materialistic, and self-absorbed members of upper class society, such as supermodels and people from old money. The pair often satirized upper class snobbery and perceived beauty.

In 1999, they released the concept album So... How's Your Girl?, which was loosely based on an episode of the Chris Elliott sitcom Get a Life entitled "The Prettiest Week of My Life." The episode also contains the origin of the name Handsome Boy Modeling School, where Chris Elliott's character enrolls to become a male model. In the album, Dan and Paul assume the characters of Nathaniel Merriweather and Chester Rockwell, respectively. A number of guest musicians appear, including Del tha Funkee Homosapien, J-Live, Sean Lennon, Miho Hatori (of Cibo Matto), Mike D (of the Beastie Boys) and Don Novello (as comic character Father Guido Sarducci).

Their second album, White People was released in November 2004. Some collaborators from the first album return, and new collaborators include RZA, Cat Power, Mars Volta, Jack Johnson, Mike Patton, Pharrell Williams, Chino Moreno, Lord Finesse, Black Sheep, and comedy actor Tim Meadows.

In 2006, Prince Paul announced his retirement from Handsome Boy Modeling School due to business conflicts with Dan the Automator.